


Daddy's Boy

by Setaeru



Category: Supernatural
Genre: Alpha Benny, Alpha Cain, Alpha Castiel, Alpha/Beta/Omega Dynamics, Alternate Universe, Blood Kink, Castiel's Handprint, Daddy Kink, Dark, Double Penetration in One Hole, Face-Fucking, Foursome - M/M/M/M, M/M, Mark of Cain, Minor Character Death, Multiple Orgasms, Omega Dean, Orgasm Delay/Denial, Pet Names, Praise Kink, Rough Sex, Serial Killers, Size Difference, Torture, Triple Penetration
Language: English
Status: Completed
Published: 2016-03-09
Updated: 2016-03-09
Packaged: 2018-05-25 16:26:39
Rating: Explicit
Warnings: Creator Chose Not To Use Archive Warnings
Chapters: 1
Words: 7,006
Publisher: archiveofourown.org
Story URL: https://archiveofourown.org/works/6202546
Author URL: https://archiveofourown.org/users/Setaeru/pseuds/Setaeru
Summary: <blockquote class="userstuff">
              <p>
  <strong>*Note: <span class="u">Contains fairly graphic torture.</span> Something you can easily skip over.</strong>
</p>
<p>Dean Winchester is the omega mate of three very intimidating alpha males; he manages to prove his worth to them, not that he really needed to, by torturing and then killing a female beta as they watch. <span class="small">And then they fuck him into the next century.</span><br/>--<br/><em>"Please-" he gasped, squirming as he embarrassingly felt his orgasm approaching. "Please- Stop- I'm gonna- Fuck," he half-moaned and half-whined, leaking a mess between his legs, from both his ass and cock. "Ah! Gonna-" No one said he could come, he couldn't- fuck. Dean quickly reached for the base of his cock with his left hand, only to have it grabbed by Cas before he could make it. "Please don't-" He opened his eyes, gasping and snapping his legs together with a wet sound, trying to somehow stall his orgasm. </em></p>
            </blockquote>





	Daddy's Boy

**Author's Note:**

> **I suggest skipping over the torture scene because it's kinda graphic, unless you're into that sort of stuff. It's been italicized, ends at the second breaker line.**
> 
> [Tumblr](http://setaeru.tumblr.com/) Ask: _hi i don't know if you use this account but i found it on your ao3 profile. can you please write a smutty oneshot with cas dean benny and cain with dean killing a girl and make it omega dean with the rest alphas and kinda detailed torture too please thank you_
> 
> To the anon who requested that, sorry for the reallllllly long wait and I hope you like it. And I hope everyone else likes it too~ :) Tell me if I have anymore tags that need to be added.
> 
> Unbetaed, unread, forgive me and enjoy! <3

**_Cain_ **

_He stood with his hands behind his back, shoulders stiff and back straight, head held high and legs spread to shoulder width. His hair was tied neatly at the nape of his neck, his blue eyes hard and calculating, lips pressed thin. He was waiting, patiently, for his mates to arrive._

_A beautiful redheaded female beta lay on a cold metal table, firmly tied down to it and gagged. She was awake and completely coherent and yet, she didn't struggle nor fruitlessly scream around her gag. She was bare of clothing, stripped for his gaze and anyone else's. She had a delectable body, something most men would beg to worship endlessly._

_She had been the same way earlier, but when he'd taken his knife and lightly cut her forearm, she had started to cry. Silently, at first, but when he'd leaned over and licked her tears up, beard scratching over her smooth face, she'd let out a sob that was sickeningly delightful. She'd closed right up when he started to lick her arm of the blood, though, which most definitely wasn't something he had liked. However, it was fine. He had a feeling she was a screamer, and by the Gods, he would make her scream until her throat was raw with agony and tears. Or maybe his omega would._

_The door screeched behind him, and he tilted his head, gaze darting to the right and staring behind himself. The door opened to reveal three men, a burly alpha with an easy grin, a lean alpha with brilliantly blue eyes and a tall omega with beautiful green eyes and a small smile. The burly alpha, named Benny Lafitte, shut the door when they all stepped into the room. The leaner alpha, Castiel, setting their bags on another metal table close to the girl._

_The omega, however, just stood there. Hesitant and worried, gaze darting around the room curiously. He suppressed a smile at the sight of him, turning to the side, so his right faced the omega. "Dean," he said softly, blinking easily as the omega's gaze snapped to him immediately. "Come here, sweet boy."_

_Dean obeyed instantly, booted feet strolling easily across the short distance between them. He came to stand just an inch away from his right arm, eyes wide and bright, an eager smile struggling to be contained. "Cain?" He muttered, cheeks darkening ever so slightly with a red tint._

_"She is yours," he said, deciding, and turning and stepping back at the same time, so he faced Dean. From the corner of his eye, he noticed Castiel open the bags and remove a saw and drill, a knife set following it, along with various other equipment. "Make me proud, Dean." He watched his omega's eyes widen further and dart between him and Benny and Castiel nervously._

_It was obvious that he was scared of messing up, of making them think less of him, or making them angry. He wanted to make them proud, always had, always desperate for the approval that had never been given to him when he had been younger. Cain wanted to reassure him, just like he knew Benny and Castiel did, but they had to be detached; they had let their omega finally see that he was worthy of them and their love._

_Benny stepped up behind Dean, placing a hand on his left shoulder. Dean swallowed and turned his head, looking at him with a terrified gaze. Cain could smell his fear, his curiosity, his excitement. It was adorable, honestly. He pushed away his sense of smell, knowing it would do him no good in such a moment, and stepped back more. He sat down on the other table, right beside a knife, and watched Benny guide Dean to stand at the girl's feet._

_Benny walked over to him and hopped up onto the table, leaning in close and relaxing. Castiel joined them a moment later, leaning heavily into Benny's side, head falling onto his shoulder as an eager smile twitched over his lips. Dean shuffled his feet, staring at the girl for a few moments. The girl lifted her head, staring at Dean before tears glazed her eyes again, but they didn't fall, not yet._

_Dean breathed deeply, trying to calm himself. The girl lowered her head, realization obviously coming over her. It was starting, and she could do nothing to stop it. Dean walked over to their table, staring down at the various devices laid out on the lengthy surface. There were endless ways he could begin this, so many things he could use to start._

_He reached out and picked up a small, thin and long knife with a thick and firm handle. He turned it over in his hands, staring at it intently. Dean also grabbed a longer knife, thicker and bigger, and walked over to the girl. He carefully pulled himself up onto the table, crawling over her naked body and resting on her hips._

_He stared down at her quietly, the knives in his hands resting on his thighs. He shifted the smaller knife to his other hand, and reached forward, pulling the gag out of her mouth and tossing it onto the floor. Dean didn't look towards them, but Cain knew he wanted to, desperately; he wanted to know if this was okay, if he could do this._

_Dean swallowed and leaned forward, bracing his arms on either side of her shoulders, he slid down closer, leaning into her exposed neck. He stayed there for a moment, nose buried in her neck, body tense and not moving. Then he sat back and smiled widely, pleased with something. He took the smaller knife and pressed the tip into the middle of her chest, pressing down lightly and dragging it towards her stomach._

_The girl gasped and tensed, tears spilling from her eyes and chest jerking with silent sobs. She wanted to beg, but she was stubborn, clearly. Dean stared at the blood in wonder then dipped his head down and licked up the mess of red he'd created between her breasts. He moaned softly, eyes falling shut as a shiver ripped through him._

_Dean opened his eyes, turning his head to look at them as he licked his reddened lips, pupils dilated with arousal. He was no doubt hard, throbbing within his loose jeans, desperate for contact on his cock; something gentle and sweet, teasing and hot. He dropped the small knife beside the girl's head with a clatter, the sound echoing through the room along with the beta's harsh breaths._

_"What's your name?" Dean asked, turning to look at her again. The girl didn't say anything, lips pressed tight and eyes dark and angry and fearful. "What is your name, beta?"_

_It took several long moments but eventually she opened her mouth and said, "Anna."_

_"Anna," Dean repeated, a pleased expression appearing. "Hello, Anna. My name is Dean."_

_"Hello, Dean," she said thickly, voice small. "Why are you doing this to me?"_

_"Because," he muttered, taking the other knife with his right hand and turning it around, staring at the gleaming metal. "You are..." He shook his head, looking back at her. "You are... absolutely... ravishing," he breathed, eyes darkening._

_"Please," she begged, hiccuping as she struggled not to sob, tears dripping down her cheeks. "Please, don't do this. Don't-"_

_"Shh," he whispered, pressing the knife to her lips, immediately silencing her. He dragged it lightly over them, then over her cheek and jaw. "Be a good girl, Anna, and don't say a word." Cain glanced at the other alphas, watching Benny palm himself lightly through his pants and Castiel nibble on his lip as they watched Dean with entranced gazes. He smiled, they were already pleased with Dean's work, and he hadn't even done much yet._

_Dean slid it over her neck, down to her collarbones and chest, over her breasts and stomach. He slid it back up to her right arm, stroking over it with the cool metal slowly. He turned it, so the tip pointed over her arm, moving it back and forth without touching her skin. He paused over her bicep, turning the blade a little and tilting his head, he looked at her face then back at her arm._

_He pressed the blade into her arm, slicing in about an inch before she let out a loud cry and jerked away, or tried to. He frowned and pressed her shoulder down with his free hand, pushing the knife deeper into her skin. Dean's lips parted at the dark red erupting from the wound, his Adam's apple bobbing as he swallowed thickly._

_He pulled the knife out and dropped it on the section of table beside her right ear, opposite the other knife, and dove his head down, lips covering the thin but deep cut and sucking softly. He sat up a second later and his gaze darted across the room to them, eyes locking with... Benny, Cain noted. Their blue-eyed blood lover sat up, eyes narrowing, but lips parting curiously._

_Dean jumped off of Anna and walked straight over to him, crawling into his lap and slotting their lips together, transferring the blood he'd sucked from Anna into his mouth. Benny moaned softly and grabbed Dean's ass, pressing their bodies together tightly. The smell of slick drifted to Cain's nose and he growled, gaining their attention._

_Dean flushed with embarrassment and immediately jumped off of Benny, fidgeting and shuffling his feet. "Sorry," he muttered, looking down at his shoes. "Didn't mean to-"_

_"Hush," Castiel reached out and swept his finger over Dean's red lips, catching a drop of blood. He brought his finger to his mouth and sucked on it, groaning quietly. "Continue, sweetheart," Castiel urged, a dark gleam entering his beautiful eyes. Dean grinned and picked up a deep scoop, gas lighter, staple gun and a cloth._

_He padded back over to Anna, setting the items beside her head before crawling back on top of her, a little higher this time. "Benny?" Dean asked, turning to look at them hesitantly. "Would you mind holding her head?" Benny glanced at him then grinned and hopped off the table, walking over and putting his large hands on either side of Anna's head, holding her still. "Thanks."_

_"No problem, cher," Benny winked, making Dean momentarily flush red. Dean grabbed the staple gun and pulled at her eyelid. She stared at him with horrified eyes, immediately trying to struggle and jerk him off but failing. The omega pressed her eyelid to her eyebrow, pulling taut and stapled it down._

_Anna cried out, tears swelling up and spilling down her face as he put in another staple before pulling the skin under her eye down towards her cheekbone and stapling that as well, he then repeated the process to the other eye. Dean set the staple gun down on the table and picked up the scoop, locking eyes with Benny for a moment and smiling sadistically._

_"Hold her tight, please," Dean said, tongue poking out of his mouth as he leaned down a little more and dug the scoop into the side of her eye. Anna screeched horridly, shaking her head against Benny's hand and failing to move it. Dean carved her eye out, popping it from the socket but leaving it attached._

_He repeated the same to the other side, then set the scoop down and took the small knife from earlier, using it to cut her eyes from her body completely. He set the eyes on the cloth he'd grabbed and took the gas lighter, igniting it and burning her eyes and the surrounding skin carefully. He didn't want her dead, he just wanted to stop the blood._

_Dean stuffed the gag back into Anna's mouth, cutting off her screams. He sighed and sat back, jumping off of her and gesturing Benny away. Benny hummed and walked back over to the table, sitting in between Cain and Castiel once more. Dean picked up the cloth with the eyes, scoop, knives, staple gun and lighter and walked over to the table, setting them down at the opposite end of the alphas._

_Dean picked up a different knife, curved and thick, blade sharp and gleaming. He walked back over to Anna, standing at her feet. He breathed deeply, looking back at his mates with eyes that showed his hesitation, but then he turned away, and he began to carve._

* * *

**_Dean_ **

_Dean was covered in blood by the time he was done, dried and fresh. Cain paced calmly beside the table, Cas sitting on the floor and leaning against one of the weapon table's legs, watching him with sharp eyes, and Benny leaned against the door, twirling a knife in his hands._

_Dean yawned and stretched, smiling but exhausted from bending over Anna's body for the last couple hours. He looked at Cain, who eyed him with a blank expression, and the smile slowly dropped from his face. Had he taken too long? Did he do too much?_

_Cain walked over to him, hand lifting and cupping his face gently. He leaned in close and pressed a kiss to his forehead, making him flush a little. "Good boy," Cain murmured, smiling against his forehead. Dean beamed, blushing deeper, and shuffled his feet shyly._

_"I'm proud of you, Dean," Cas said as he stood up. He walked over and hugged Dean from the side, nuzzling his cheek and kissing his ear. "Very proud, baby boy." Dean squirmed in his arms, embarrassed to be hugged so sweetly._

_Benny slid up behind him without him noticing, arms slipping around his waist and pulling him in close. He nuzzled the bite on the left side of Dean's neck, his bite. "Extremely proud of you, cher."_

_"I'm tired," he said slowly, hoping they wouldn't get mad. He'd been standing and methodically working for a while now, it was okay that he admitted he was tired, right? Cain smiled, warm, and nodded._

_"Castiel and I will dispose of the body, Benny will take you home for a shower and nap. We'll be home in about three hours, perhaps four," Cain said, heading over to the table with their supplies. "Be ready for us." There was a deeper meaning to that, one Dean was most definitely not complaining about._

_Cas kissed his cheek and kissed Benny on the lips, stepping back and walking over to Cain. Benny took his hand and led him to the door, pulling it open and guiding him outside into the cool evening air. Benny shut the door and guided him over to his car, a beautiful sleek black Mustang. They climbed in and then they headed home._

* * *

Dean moaned and shifted over, yawning and stretching tiredly. He blinked his eyes open, staring at the white ceiling of their bedroom. His whole body was sore but he was okay, it wasn't too bad. He looked around him at his mates and frowned. He remembered Cain trying to wake him up last night but he'd been so tired, he'd just whacked his hand away and turned over.

He hoped he wasn't mad at him, desperately hoped. He would have to apologize for his behavior but he didn't want him mad. Dean crawled out of bed and walked into the bathroom, quickly peeing and washing his hands before cleaning his face and brushing his teeth. He headed downstairs after to start making breakfast.

Dean turned on the coffee maker then decided to make pancakes, quickly making the batter and heating up the plate. He took some fresh fruit from the fridge and started chopping it into smaller pieces, putting them into a bowl. He set butter and syrup and whipped cream on the table between putting chocolate chips on some of the pancakes and flipping them. By the time he was done making breakfast, his alphas were padding into the room tiredly.

"Morning," he said, smiling at them. Benny kissed him gently and sweetly while Cas went straight for the coffee maker, grabbing a mug and filling it and gulping it down. Cain slid an arm around him when Benny went to sit down, leaning closer and nipping his ear sharply. He whimpered and ducked his head, unable to look at him. "I'm sorry, alpha."

"Mhmm. Good morning, Dean," Cain huffed, cinnamon toothpaste coating his breath. His alpha licked the spot he'd bit gently, coating it in a thin layer of saliva. "Let's eat," he said, stepping away and tugging Dean towards the table. Dean sat between Cain and Cas as they ate, Benny on Cas's other side.

Cas reached over and fed him a slice of strawberry, nuzzling his cheek and pressing little kisses to his jaw. "Did you have fun last night, my love?" Cas asked, an arm slipping onto the back of Dean's chair. Dean nodded, swallowing his bite before speaking, knowing it would only get him in trouble if he spoke with his mouth full.

"Yeah," he said. "It was fun. And she deserved it for raping that boy." Cas smiled and lifted his arm from the chair, sliding his hand into Dean's hair and massaging lightly. He was barely resisting a purr, so he turned away and stared down at his plate of pancakes. Cas's fingernails scratched over the nape of his neck, sending a shiver down his spine, then slid back up, teasing his scalp.

"We're glad, Dean," Benny said, setting his fork down on the table. "I'll clean up but I need to make a call first." Benny stood and kissed Cas's head as he walked out of the room.

"Dean," Cain said, turning to look at him, a strange little sparkle in his sharp blue eyes. "Go wait for us in the playroom." Cain dug into his right pocket and pulled out a pair of keys, handing them to Dean.

Dean swallowed, nervous. He didn't say anything though, and just set his fork down in his empty plate, took the keys and walked to the basement door. He unlocked it with one key, stepping onto the stairs and leaving it ajar. An LED light guided him down the stairs and to a small space with a freezer and two doors.

One door held a medium sized game room with a pool table, a huge television and multiple game consoles. The second door, the one with the lock, was their playroom. Dean stuck the second key in the lock and turned it, unlocking the door and opening it. He stepped inside and flicked the dimmer light on, making sure it was fairly low so it didn't hurt the eye.

The room was huge and completely covered in deep grey pads, blocking out sound and making the whole room a huge cushion, even the floor was covered in it. There was a huge bed with dark red sheets and grey and white pillows, made of steel but covered by pillow soft fabric. There were toys along the walls and in drawers, and a Saint Andrew's cross to the right of the bed. There was a sex swing, spanking bench, cock and ball pillory - which he hated so goddamn much, something Cain called a fuck bench that they'd never used before, and a steel puppy cage.

Dean stripped off his clothes, setting them in a neat little folded pile by the door. He walked into the middle of the room and turned to face the door, dropping to his knees and spreading his legs apart, moving his hands behind his back and grasping his left wrist with his right hand. He lowered his head and breathed deeply to keep himself calm.

He waited, watching his flaccid cock steadily grow hard and smelling his sweet slick as it slowly dripped out of him and the smell spread throughout the room. Dean shifted occasionally, listening eagerly for the sound of steps but hearing nothing at all, even with the door wide open. 

It was about twenty minutes later, when his knees were sore and his shoulders hurt, that he heard three familiar pairs of feet coming down the stairs. He straightened his body eagerly, biting the inside right corner of his mouth to keep from making any sounds, struggling to breath deeply and evenly. The door shut quietly as his alphas entered the room and slowly stalked towards him.

He barely swallowed a whimper when Cain's familiar legs appeared in front of him. He sniffed lightly and squirmed when he smelt alpha arousal, a heady and musky scent, mixed with their own unique ones. His ass was embarrassingly leaking onto the grey cushion and his lower legs but he could do nothing about it.

"Dean."

"Yes, daddy?" he muttered, flushing a little shyly when Benny huffed in amusement.

Cain groaned and crouched in front of him, hand sliding into his hair quickly and pulling, making him tilt his head back and partly arch his back as he gasped. Cain leaned in and kissed him, deep and long and perfectly filthy. Dean moaned and lifted himself up, arching his back further and eagerly returning the rough kiss. His cock twitched between his legs and his ass leaked more slick but he didn't care, because his daddy's hands were on him and he was being kissed.

Cain pulled him back, tugging on his hair when he tried to follow. He let go and massaged his abused scalp gently. He trailed the hand to his cheek, leaning in again and nuzzling their noses together. He took hold of his right arm with his other hand, bringing it up and turning his attention to the unique mark on his inner forearm, just below his elbow crease.

He licked the mark carefully, making Dean moan and shift. It was his mating mark, something he'd given Dean when they'd bonded, and it was _extremely_ sensitive - but only to him. It was a dark red, similar to a burn, and bumpy; it was divided into three parts, the largest straight with a curved top, followed just below it with two drop looking marks. His alpha sucked lightly on the mark, forcing a whine from his throat.

Dean didn't notice Cas sliding up beside him until his mouth was working over his left shoulder where he'd also left his mark, in the form of his hand. He moaned loudly, tilting his head back and closing his eyes, hips twitching and cock throbbing. They both licked and sucked mercilessly at the marks, distracting him from Benny, who knelt behind him.

Benny rubbed his hands around his sides and over his abdomen, hands rubbing over his nipples gently, teasing and pulling and rubbing. He licked at his bite mark - his mating mark, licking and sucking gently on it.

"Please-" he gasped, squirming as he embarrassingly felt his orgasm approaching. "Please- Stop- I'm gonna- Fuck," he half-moaned and half-whined, leaking a mess between his legs, from both his ass and cock. "Ah! Gonna-" No one said he could come, he couldn't- fuck. Dean quickly reached for the base of his cock with his left hand, only to have it grabbed by Cas before he could make it. "Please don't-" He opened his eyes, gasping and snapping his legs together with a wet sound, trying to somehow stall his orgasm. 

Benny removed his mouth from his mark, trailing kisses up to his ear. "Come," he ordered, voice deep and strong and husky. Dean sobbed a little, hips bucking sharply as thick and long spurts of come came out of his cock, his ass squirting out slick as well. He moaned desperately, shuddering as they continued to tease him and the marks.

They didn't stop until he was hard again, throbbing and needy. They sat back and stood, walking around him in a circle. Dean dropped his hands between his knees, just in front of the mess he'd just made, and panted, shoulder and forearm and neck throbbing with pleasure.

"Clean up your mess, pet," Cas said, stopping to his left and crouching, hand grabbing his hair and pulling him backwards. He obeyed, crawling backwards and breathing hard. Cas forced his head down and he obediently lapped up the sweet tasting mess he'd made on the floor. Cas pulled him up roughly when he was done, forcing his head to the left and kissing him, tasting Dean's slick and come. He licked his mouth and pulled back, grinning darkly. "Good boy."

Dean whined, stomach fluttering at the praise. Benny came up on his other side, pulling him in close and picking him up bridal style. He clung to him as he carried them over to the bed, sitting down with Dean curled up in his lap. "You did so well yesterday, Dean," Benny said, rubbing his head and lightly scratching behind his ear. "Today we're going to reward you. What would you like, baby?"

Dean blushed and curled in closer, burying his face in Benny's neck and scenting him. "I wanna- I wanna be fucked like a dirty whore," he muttered it but it was loud enough that they all heard him. Cas laughed, sounding so pleased and sadistic and he shuddered, squirming in Benny's lap.

Benny nudged his head away from his neck then buried his own in Dean's, teeth grabbing onto some flesh, biting and pulling at his skin. Dean moaned, dropping his legs to the ground and shifting in his lap. Benny pulled back and turned him so he sat with his back to the alpha's chest, pulled close and held tight. 

Castiel knelt in front of him, spreading his legs apart. He leaned forward and licked the head of Dean's cock, wrapping his lips around it and sucking hard. Dean groaned, arching his back and twitching his hips forward, slick dripping out of him and soaking into Benny's pants. Castiel sucked more of him into his mouth, cheeks hollowing as he flicked his eyes up and locked gazes with Dean.

Dean squirmed in Benny's lap, feeling the alpha lick at his neck while Castiel worked over his small cock, sucking and licking and carefully, very gently, dragging his teeth over his cock. He whimpered, thighs quivering as he felt his rapidly approaching orgasm tighten something in his belly.

"Gonna come, gonna come," Dean gasped, panting softly and letting the back of his head drop onto Benny's shoulder.

"Don't you dare," Cain growled darkly. Dean whimpered and shook his head, trembling hands reaching down to grab Benny's pants.

Benny hummed softly, hands rubbing up and down his chest, fingernails scratching over his nipples and sending jolts of pleasure through him. Dean wiggled, squeezing his eyes shut and breathing deeply, trying to hold his orgasm back and ignore the hot mouth wrapped around his cock and the hands teasing his nipples.

"P-please," he bit his lip, curling his toes and desperately trying to get away from Castiel's mouth.

"Come," Benny murmured in his ear, teasing and light, but commanding and heavy.

"N-no," Dean whimpered pitifully, sucking in his stomach and holding his breath, biting harder on his lip. "Can't- can't."

"Come on, Dean," Castiel pulled off his cock, licking his spit coated lips. "Come for me." He wrapped his lips around the head, hand massaging his balls gently.

He probably could come, especially since Benny _and_ Castiel gave him permission. But there was a little bit of a hierarchy within them. Dean was their omega and submissive, so he came last on the order chain. One up from him was Benny, after that Castiel, and at the top, making majority of their decisions, was Cain. He always wanted to please his daddy more than he did Castiel or Benny, so he refused to come if Cain said he couldn't and the others said he could.

But it wrecked with him when moments like this happened, made him conflicted. "Please, daddy," he whined, clenching his ass and rutting against Benny's thighs, fucking into Castiel's willing mouth. "Please, please. I'll- I'll be good. _Daddy._ "

Benny's arm slipped around his waist, his other pressing against his chest while the hand connected to said arm wrapped around his throat. Dean moaned, feeling himself being forcefully pressed against Benny's body.

Cain stepped up behind Castiel, legs pressing against the man's back, and cupped Dean's cheek, lifting his head and locking eyes with him. "Come for me, sweetheart," Cain said softly, eyes dark. Dean whimpered as he felt his orgasm take over him, his back arching as much as it could with Benny forcing his back against his chest. He couldn't look away from Cain as he came into Castiel's mouth, eyes filling with tears as blinding pleasure overtook his body.

"Daddy," he mewled, hands shaking. Castiel pulled off his cock with an obscene pop, a pleased expression on his face. Dean swallowed dryly, cock throbbing with aftershocks of pleasure. Cain licked his lips slowly, a small smile stretching his lips.

"Good boy," he murmured, and Dean purred at the praise, biting his lip. "Get off of Benny and lay on your stomach on the bed." Benny released him and Dean moved to the side, crawling onto the bed and laying on his stomach with his legs slightly spread and his arms laying at his sides. "So good," Cain said.

Dean rubbed his face against the soft sheets, relaxing into the mattress with a quiet sigh. Dean heard some shifting behind him but didn't bother turning and looking. He closed his eyes and waited, being as patient as he could for his mates to crawl onto the bed or order him to do something, even say anything. None of that came. So he stayed still and breathed as slowly and calmly as he could, forcing his body to remain relaxed and at ease even as he listened to his mates walk around the room.

"Dean," Cain said, and he opened his eyes, tensing when he realized Cain was directly in front of his face. "Sit up so I can lay underneath you." Dean frowned but didn't say anything, pushing himself up and crawling backwards. Cain slid onto the bed and lay down with his head on a pillow, guiding Dean onto him so he could straddle his hips.

Dean moaned as their cocks brushed, his quickly hardening again. His ass leaked more slick onto the bed, and maybe onto Cain's thighs as well. "Spread your legs more," Castiel said, crawling onto the bed as well. Dean shifted his legs further apart as Cain spread his as well.

He glanced back at Castiel, feeling his heart beat faster as he realized what was going to happen. Castiel grinned at him and kissed him on the lips, plunging his tongue into Dean's mouth. Castiel brushed his fingers over Dean's wet hole, easily pushing one inside of him. Dean squirmed and rocked back onto that finger, groaning into Castiel's mouth as his cock rubbed over Cain's again.

Castiel pushed another finger into him, brushing over his prostate and sending shocks of pleasure through him. Dean shuddered and bit Castiel's bottom lip, sucking on it lightly and pulling back, letting it drag through his teeth. Castiel groaned and dropped his head, lips pressing against Dean's shoulder.

Castiel pulled his fingers from inside of Dean, pushing him up higher and reaching between Dean's legs. Dean looked down and watched him wrap his hand around Cain's cock, stroking it once, twice, and lining it up with Dean's hole. Dean groaned and slowly rocked down onto Cain's cock, clenching around him tightly as his body rapidly adjusted to the intrusion.

Castiel let go and grabbed his hips, holding him in place and grinding his cock against Dean's hole and the base of Cain's cock. He moaned in Dean's ear, breathing harder than normal. Dean tilted his head back and rested it on Castiel's shoulder, looking up at the ceiling for a moment. Cain slid a hand over his front, nails scratching his belly lightly and making him pull his stomach in.

The bed dipped as Benny crawled onto it, sliding up by Cain's side and leaning down, pressing his lips to Cain's in a deep kiss. Dean's eyes widened slightly, his breath catching as he watched his mates share a filthy kiss right in front of him. Benny pulled back and shot him an amused look, licking his lips as his eyes raked over his exposed front.

Benny carefully stood on the bed, standing on either side of Cain's body and close to Dean's knees. The bed dipper where he stood and pushed Dean forward a little more but he didn't mind. He stared up at Benny, feeling Castiel nudge a finger against his hole, rubbing his stretched rim. Benny grinned and brushed the head of his cock against Dean's lips, smearing precum across them.

Castiel pushed his finger in alongside Cain's cock, twitching it around and making Dean moan deeply. "So tight," Cain twitched his hips, groaning quietly. His cock pulsed inside of Dean, sending a shiver racing over Dean's spine. Castiel pushed another finger inside, making Dean tense and hiss slightly at the slight pain the action gave. 

His body was quick to adjust to it though, ass clenching around the fingers and Cain's cock, greedily pulling them further inside of his hole. "Please," he muttered, leaning forward and resting his head against Benny's thigh, turning it and nuzzling his nose and lips over the man's balls. "Just slide in. I'm fine."

"Are you sure?" Castiel's voice seemed rougher and deeper than usual, it made Dean's cock twitch. Dean nodded, looking up and locking eyes with Benny as Castiel removed his fingers and pressed the head of his cock against his hole. He inhaled sharply as Castiel forced his cock inside, not stopping until he was fully buried inside of Dean alongside Cain.

Cain arched his back and pressed his hips up, Castiel cursing softly, and Dean felt his eyes sting with tears at the sharp pain that appeared in his ass. He tensed and waited a few moments, breath held, as his body adjusted to the two cocks buried in his ass. They'd done this before, but not recently, so it was much tighter than last time.

"You okay, chief?" Benny murmured, running a hand through his hair comfortingly. Dean swallowed and exhaled, inhaling right after and trying to breath normally. He nodded and shifted, biting his lip as he felt Cain's cock press into his prostate.

Castiel shifted a little, bending him forward, forcing Benny to take a small step back so his groin wasn't pressed directly into Dean's face. Dean glanced down when he saw something move, and watched as Cain dragged his hands over Benny's calves, nails dragging over his skin. He swallowed and pressed his hands to Cain's chest, scratching over the soft hair covering his skin.

He looked up again, locking eyes with Benny, and opened his mouth, letting the man push his cock into his mouth. He swallowed and relaxed his throat, feeling Benny drove in all the way easily. The man groaned loudly above him, eyelids going down to half-mast, and a small, pleased smile appearing. "So warm, cher," he purred, pulling on Dean's hair while pushing his face closer to his crotch.

"He's always warm," Castiel muttered, rocking his hips back an inch and sliding back in. Cain and Dean and Castiel moaned in unison, Dean clenching tightly around both of them. Benny muttered a curse as Dean's throat fluttered around his cock, his hips moving back, cock dragging out of Dean's throat. "And tight."

Dean felt his cheeks burn slightly, and closed his eyes so he wouldn't have to look at Benny's amused blue ones. Cain's familiar calloused hand wrapped around his cock, gentle and teasing, stroking him slowly and loosely. Benny slowly fucked in and out of his mouth, not pulling out or pushing in more than an inch or two, and Castiel rocked his hips, fucking in and out of Dean slowly.

Cain pressed his hips up, shifting his legs and bracing them as he began to slide out and in of Dean, falling into a slow and steady rhythm with Castiel; Castiel would pull out and Cain would slide in, and they would do it over and over again, keeping it slow and teasing. Dean arched his back and moaned around Benny, letting the man fuck his throat deeply and carefully.

It wasn't long before the feel of Cain's cock rubbing over his prostate was too much and his orgasm was approaching, his cock swelling and throbbing with pleasure and need. He tapped Cain's abdomen, silently telling him he was close. Cain replied by squeezing his cock tightly and moving his hand faster over Dean's member.

He whined around Benny, choking slightly, and bucked into Cain's hand, ass fluttering around both Cain and Castiel's cocks. Benny hooked his thumbs at the corners of Dean's mouth and started fucking into his throat roughly, uncaring as Dean choked and gagged slightly around him before calming down and just letting it happen.

Castiel pulled out to the tip and slammed back into him, Cain not moving more than a couple inches in and out of him as Castiel fucked him roughly. He cried out around Benny, cock twitching as little spurts of come dribbled out the tip of his cock and over Cain's hand. He whimpered softly, rocking into Cain's hand slowly.

Cain's other hand rubbed his side, squeezing lightly, calming him down from his orgasm. Benny muttered something above him, and it made Cain laugh, but Dean wasn't paying enough attention to hear it. Castiel held his hips in a bruising grip and fucked him roughly, pressing Cain's cock insistently on his prostate, sending bolts of pleasure to his cock and forcing it to harden again.

He pulled back, forcing Benny to remove his cock from his mouth. "Please," he muttered roughly, throat throbbing with each beat of his racing heart. " _Please._ "

Benny forced his cock back into Dean's mouth, keeping his head still and fucking in and out roughly, ignoring Dean's whimpers and just taking his pleasure without a care. Castiel did the same to his ass, hips jerking back and forth as he fucked him forward. Cain was the only one who stroked his cock and rubbed his side gently, cock slowly and methodically moving in and out of Dean's wet hole.

He felt Castiel's knot slowly forming, his cock swelling. Cain grunted and started thrusting into him faster, chasing his own orgasm. Benny was oblivious to them all, eyes squeezed shut as he roughly pounded into Dean's mouth, making him choke every few seconds. Dean bucked into Cain's hand, moaning around Benny as he felt yet another orgasm building rapidly within his body.

Castiel was holding back, but Benny was definitely not. He fucked Dean's mouth as his knot swelled, forcing Dean to cough around him, and pressed forward, locking his knot inside of Dean's mouth as he came down his throat, moaning deeply and loudly, hips twitching. Cain shifted and gripped his very upper thighs, driving his hips up into him and pounding his prostate.

Dean looked up at Benny, locking eyes with the man. Benny had a pleased expression on his face, but he was also frowning because he probably realized he was kind of stuck there until his knot went down. Dean heard Castiel let out a sound that was a mix of a whimper and a moan and push forward as his knot swelled. That made Cain press up into Dean as well and moan as his did as well.

Dean tensed as he was stretched painfully around two pulsing knots, his hole throbbing with pain. He felt Cain jerk him off quickly, urging him to come again, but he couldn't really bring himself to. "Come on, sweetheart," Cain said quietly. "Come for daddy."

Dean whimpered around Benny's cock, pushing into Cain's hand desperately. He curled his toes as he felt his orgasm quickly approaching, lower abdomen tightening and cock swelling slightly, balls throbbing. He arched and bucked sharply as he came on Cain's chest, choking around Benny and forcing himself to breath through his nose the best he could with Benny's cock buried in his throat.

He slumped back against Castiel, feeling thick ropes of semen coating his insides as both Cain and Castiel came inside of his hole. "So good," Castiel muttered, burying his face in Dean's neck and panting quietly.

None of them moved or said another word the whole time it took for their knots to go down, only slipping out slowing and gently once they could. Benny disappeared the second he could, cleaning off and going to find something. Cain just cleaned himself and returned to his spot in the middle of the bed, leaning against the headboard this time.

Castiel didn't bother pulling out of him, just sat back and pulled Dean with him so he sat in his lap. He wrapped his arms around Dean's waist and nuzzled his shoulder and nape, contentment rolling off him in waves. Dean let himself be held, relaxing into Castiel and closing his eyes. He was kind of cold and tired, and he really wanted to clean up and take a nap but it was so nice to have Castiel's arms around him.

Eventually though, Cain nudged them apart and cleaned them both off thoroughly, pushing them under the covers. They went willingly, curling up under the sheets together just as Benny returned with water and some fruit, which included delicious looking chocolate covered strawberries. They curled up under the covers together and fed each other little bits of fruit, occasionally drinking from their bottles of water.

Dean slid down further under the sheets, closing his eyes and yawning. A hand rubbed through his hair, calming and tender. "Sleep," Cain muttered, pressing a kiss to his temple.

"Okay, daddy," he murmured sleepily, ignoring Benny's amused noise at the name and Castiel's little tap on his nose. He shut his eyes and slept.

**Author's Note:**

> Hope you enjoyed that~ Comments and kudos are welcomed and appreciated! <3


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